Episode 72: Risk in Every Form with Greg Winchester

  

What does it take to keep saying yes to risk, in the boardroom, on the trail, and across all seven continents, for forty years and counting?

Greg Winchester calls himself an armchair explorer, but the title sells him short. Over a 40-plus-year career in commercial real estate, he has worked through the savings and loan crisis, the 2008 financial crisis, and COVID, first as a banker, then as a co-owner, and today as an investor through his family office, Summit Investors. In 2003, he and two partners bought their company from its founders in a management buyout, personally guaranteeing the entire debt with 300 employees and no safety net. As Greg puts it, it was like walking to the end of the diving board and jumping, hoping there was water below.

A lifelong Boy Scout who fell in love with the outdoors in the Roan Highlands of North Carolina, Greg went on to serve on the board of the Appalachian Trail Conservancy and to build a life of generosity that reaches all seven continents, inspired by the book Seven Summits. From an orphanage in Bolivia to a pastors’ training center in Uganda, a nearly thousand-year-old cathedral in Winchester, England, and Sir Ernest Shackleton’s grave on South Georgia Island near Antarctica, he and his wife set out to support smaller, lesser-known nonprofits and build real relationships, not just write checks.

In this conversation, Josh and Greg trace the many forms risk can take. They dig into why leverage is a two-edged sword, how diversification and dry powder let you run into the fire when others are running out, why your gut becomes a kind of superpower after twenty years in any arena, and how setting goals every year since his twenties shaped a life of purpose. Greg also shares the two questions a pair of mentors asked him in his mid-fifties, what is a noble cause you can get involved with, and what do you actually want to do, and why finishing well may be the greatest adventure of all.

         00:00  An armchair explorer who spent forty years navigating real estate’s biggest crises

         03:00  Stumbling into commercial real estate from a bank management trainee program

         06:00  The 2003 management buyout: 300 employees and everything personally guaranteed

         12:00  Jumping off the high dive and hoping there is water below

         14:00  A lucky break, a termination fee, and the real mix of hard work and luck

         17:00  Three things that get people in trouble: cycles, capital structure, and diversification

         20:00  Running into the fire in 2008 and why leverage is a two-edged sword

         23:00  The gut instinct you earn after twenty years in any arena

         25:00  Seven Summits and a vision to serve nonprofits on all seven continents

         29:00  Winchester Cathedral, a 950-year-old Bible, and Shackleton’s grave near Antarctica

         38:00  What rises to the top: relationships, faith, family, and friends

         40:00  A Boy Scout in the Roan Highlands and a lifelong love of the trail

         46:00  Moving toward something, not away, and setting goals every year since his twenties

         50:00  Finishing well and the two questions that reshaped Greg’s second act

Here are the people and organizations Greg mentioned in this episode:

•    Summit Investors, his family office investing in real estate across the Sun Belt

•    Auburn University Master of Real Estate Development program, where he serves as an adjunct and industry connector

•    The Appalachian Trail Conservancy, where he served on the board

•    The South Georgia Heritage Trust, stewards of the historic church and museum on South Georgia Island

•    The National Christian Foundation, which helped guide his international giving

Josh’s free resource for everyday explorers is packed with practical insights on planning for any adventure, big or small, minimizing trail waste along the way (yes, that means taxes), and living with confidence toward whatever is most meaningful to you. It also includes key takeaways from recent On Adventure guests to help inspire your next steps.

Grab your copy at ridgelinewealthadvisors.com.

Hosted by Josh Self, financial advisor and everyday explorer.

•    Subscribe on YouTube, Spotify, Apple Podcasts, and all major streaming platforms

•    Follow on Instagram for short-form clips and behind-the-scenes content

•    Connect on Facebook: On Adventure Podcast with Josh Self

•    Connect on LinkedIn: Josh Self

•    If this episode resonated with you, leave a review and share it with someone who needs to hear it

Check out this episode!